JP2014501269A5 - - Google Patents
Download PDFInfo
- Publication number
- JP2014501269A5 JP2014501269A5 JP2013546715A JP2013546715A JP2014501269A5 JP 2014501269 A5 JP2014501269 A5 JP 2014501269A5 JP 2013546715 A JP2013546715 A JP 2013546715A JP 2013546715 A JP2013546715 A JP 2013546715A JP 2014501269 A5 JP2014501269 A5 JP 2014501269A5
- Authority
- JP
- Japan
- Prior art keywords
- urea
- quinolin
- pyridin
- pyran
- heterocyclic compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 36
- 229910052739 hydrogen Inorganic materials 0.000 claims 21
- 239000001257 hydrogen Substances 0.000 claims 21
- -1 C 1 -C 6 -alkoxy Chemical group 0.000 claims 17
- 150000002431 hydrogen Chemical class 0.000 claims 15
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 229910052757 nitrogen Inorganic materials 0.000 claims 13
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 10
- 125000005842 heteroatom Chemical group 0.000 claims 10
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 9
- 239000002253 acid Substances 0.000 claims 9
- 150000001204 N-oxides Chemical class 0.000 claims 8
- 125000003118 aryl group Chemical group 0.000 claims 8
- 229910052760 oxygen Inorganic materials 0.000 claims 8
- 239000000651 prodrug Substances 0.000 claims 8
- 229940002612 prodrug Drugs 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 8
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 8
- 229910052717 sulfur Inorganic materials 0.000 claims 8
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 7
- 125000000623 heterocyclic group Chemical group 0.000 claims 7
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 6
- 125000001424 substituent group Chemical group 0.000 claims 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 5
- 125000001072 heteroaryl group Chemical group 0.000 claims 5
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 5
- 229920006395 saturated elastomer Polymers 0.000 claims 5
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 4
- 239000004202 carbamide Substances 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 208000035475 disorder Diseases 0.000 claims 4
- 102000019058 Glycogen Synthase Kinase 3 beta Human genes 0.000 claims 3
- 108010051975 Glycogen Synthase Kinase 3 beta Proteins 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims 3
- 230000000694 effects Effects 0.000 claims 3
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 claims 3
- 230000002285 radioactive effect Effects 0.000 claims 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 claims 3
- VQPBIJGXSXEOCU-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 VQPBIJGXSXEOCU-UHFFFAOYSA-N 0.000 claims 2
- GWCWCWXMAZCRIV-UHFFFAOYSA-N 1-[6-(3,4-dihydro-2h-pyran-5-yl)pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1=COCCC1 GWCWCWXMAZCRIV-UHFFFAOYSA-N 0.000 claims 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 2
- 125000002393 azetidinyl group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 208000026106 cerebrovascular disease Diseases 0.000 claims 2
- 150000001975 deuterium Chemical group 0.000 claims 2
- 229910052805 deuterium Inorganic materials 0.000 claims 2
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 claims 2
- 125000004655 dihydropyridinyl group Chemical group N1(CC=CC=C1)* 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 208000014674 injury Diseases 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 125000002757 morpholinyl group Chemical group 0.000 claims 2
- 125000003566 oxetanyl group Chemical group 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 125000004193 piperazinyl group Chemical group 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 2
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 2
- 239000000126 substance Substances 0.000 claims 2
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 claims 2
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims 2
- 230000008733 trauma Effects 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- HUIGDQIGGTVHLC-UHFFFAOYSA-N 1-(1,5-naphthyridin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC=CN=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 HUIGDQIGGTVHLC-UHFFFAOYSA-N 0.000 claims 1
- NUVBOUNAXOEMGL-UHFFFAOYSA-N 1-(5,8-difluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=C(F)C2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 NUVBOUNAXOEMGL-UHFFFAOYSA-N 0.000 claims 1
- KJDGNNMYOYVDES-UHFFFAOYSA-N 1-(6,8-dichloroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(Cl)=CC(Cl)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 KJDGNNMYOYVDES-UHFFFAOYSA-N 0.000 claims 1
- YVCQZVBSYKUTNJ-UHFFFAOYSA-N 1-(6,8-difluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(F)=CC(F)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 YVCQZVBSYKUTNJ-UHFFFAOYSA-N 0.000 claims 1
- AUBIMDGQGZMWTM-UHFFFAOYSA-N 1-(6,8-difluoroquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C12=CC(F)=CC(F)=C2N=CC=C1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 AUBIMDGQGZMWTM-UHFFFAOYSA-N 0.000 claims 1
- PYOMPXLAYCWFPK-UHFFFAOYSA-N 1-(6-bromoquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(Br)=CC=C3N=CC=2)=N1 PYOMPXLAYCWFPK-UHFFFAOYSA-N 0.000 claims 1
- HXBDFOQTPGIDNA-UHFFFAOYSA-N 1-(6-cyclopropylpyrazin-2-yl)-3-(6-piperidin-4-ylquinolin-4-yl)urea Chemical compound C=1C=NC2=CC=C(C3CCNCC3)C=C2C=1NC(=O)NC(N=1)=CN=CC=1C1CC1 HXBDFOQTPGIDNA-UHFFFAOYSA-N 0.000 claims 1
- OKGRTJOEILSKSR-UHFFFAOYSA-N 1-(6-cyclopropylpyrazin-2-yl)-3-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]urea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=NC=3)C3CC3)C2=C1 OKGRTJOEILSKSR-UHFFFAOYSA-N 0.000 claims 1
- JDLZNEXCJIZHBW-UHFFFAOYSA-N 1-(6-piperidin-4-ylquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2CCNCC2)=N1 JDLZNEXCJIZHBW-UHFFFAOYSA-N 0.000 claims 1
- RISTYTNTGUCKRV-UHFFFAOYSA-N 1-(6-piperidin-4-ylquinolin-4-yl)-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC=C(C3CCNCC3)C=C2C=1NC(=O)NC1=CN=CC=N1 RISTYTNTGUCKRV-UHFFFAOYSA-N 0.000 claims 1
- YYJKBJITPDPGDD-UHFFFAOYSA-N 1-(7-bromoquinolin-4-yl)-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(Br)C=C3N=CC=2)=N1 YYJKBJITPDPGDD-UHFFFAOYSA-N 0.000 claims 1
- VDEZAETUSYBUSQ-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(oxan-3-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCCOC1 VDEZAETUSYBUSQ-UHFFFAOYSA-N 0.000 claims 1
- OVIADVAXXQTSSR-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 OVIADVAXXQTSSR-UHFFFAOYSA-N 0.000 claims 1
- RLJBDBYYVSSBOT-UHFFFAOYSA-N 1-(7-methoxyquinolin-4-yl)-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC1=CN=CC=N1 RLJBDBYYVSSBOT-UHFFFAOYSA-N 0.000 claims 1
- OHHJJQZGSOYSCF-UHFFFAOYSA-N 1-(8-chloro-6-methylquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(C)=CC(Cl)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 OHHJJQZGSOYSCF-UHFFFAOYSA-N 0.000 claims 1
- CINSMAXRSWIPNW-UHFFFAOYSA-N 1-(8-chloroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(Cl)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 CINSMAXRSWIPNW-UHFFFAOYSA-N 0.000 claims 1
- JQJSZQPPZOVZSA-UHFFFAOYSA-N 1-(8-cyanoquinolin-4-yl)-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=C(C#N)C=CC=C2C=1NC(=O)NC1=CN=CC=N1 JQJSZQPPZOVZSA-UHFFFAOYSA-N 0.000 claims 1
- WMDXIIORGIWVQV-UHFFFAOYSA-N 1-(8-fluoro-6-methoxyquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C12=CC(OC)=CC(F)=C2N=CC=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 WMDXIIORGIWVQV-UHFFFAOYSA-N 0.000 claims 1
- MIBNRIDIGPQNKR-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-(6-piperidin-4-ylpyridin-2-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCNCC1 MIBNRIDIGPQNKR-UHFFFAOYSA-N 0.000 claims 1
- WSNGAJHTEQWBIM-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[5-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=C1)=CC=C1C1CCOCC1 WSNGAJHTEQWBIM-UHFFFAOYSA-N 0.000 claims 1
- CJMDXGWKXLQJEY-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(1-propan-2-ylpiperidin-4-yl)pyridin-2-yl]urea Chemical compound C1CN(C(C)C)CCC1C1=CC=CC(NC(=O)NC=2C3=CC=CC(F)=C3N=CC=2)=N1 CJMDXGWKXLQJEY-UHFFFAOYSA-N 0.000 claims 1
- XGYJOSADRJVTBY-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(oxan-3-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCCOC1 XGYJOSADRJVTBY-UHFFFAOYSA-N 0.000 claims 1
- LMBZXVCPBNGXGR-UHFFFAOYSA-N 1-(8-fluoroquinolin-4-yl)-3-[6-(oxan-4-yl)pyridin-2-yl]urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1CCOCC1 LMBZXVCPBNGXGR-UHFFFAOYSA-N 0.000 claims 1
- RMWWSSJQQBSPNH-UHFFFAOYSA-N 1-[6-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CCNCC=2)=N1 RMWWSSJQQBSPNH-UHFFFAOYSA-N 0.000 claims 1
- YCEGRQBTGLDCDA-UHFFFAOYSA-N 1-[6-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1N(C)CCC(C=2C=C3C(NC(=O)NC=4N=C(C=CC=4)C(F)(F)F)=CC=NC3=CC=2)=C1 YCEGRQBTGLDCDA-UHFFFAOYSA-N 0.000 claims 1
- VHYMKHPSLVPMPC-UHFFFAOYSA-N 1-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 VHYMKHPSLVPMPC-UHFFFAOYSA-N 0.000 claims 1
- FQVMTXVNXUTWIN-UHFFFAOYSA-N 1-[6-(1-methylpiperidin-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C1CN(C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 FQVMTXVNXUTWIN-UHFFFAOYSA-N 0.000 claims 1
- QFLPJUZAYALTDE-UHFFFAOYSA-N 1-[6-(2,5-dihydro-1h-pyrrol-3-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CNCC=2)=N1 QFLPJUZAYALTDE-UHFFFAOYSA-N 0.000 claims 1
- HDQBKWBMALHQDI-UHFFFAOYSA-N 1-[6-(3,4-dihydro-2h-pyran-5-yl)pyridin-2-yl]-3-(7-methoxyquinolin-4-yl)urea Chemical compound C=1C=NC2=CC(OC)=CC=C2C=1NC(=O)NC(N=1)=CC=CC=1C1=COCCC1 HDQBKWBMALHQDI-UHFFFAOYSA-N 0.000 claims 1
- DSWADQAUCOSMPB-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]-3-(1,5-naphthyridin-4-yl)urea Chemical compound C=1C=NC2=CC=CN=C2C=1NC(=O)NC(N=1)=CC=CC=1C1=CCOCC1 DSWADQAUCOSMPB-UHFFFAOYSA-N 0.000 claims 1
- BYKSEVADXIBXTH-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1=CN=C2C(F)=CC=CC2=C1NC(=O)NC(N=1)=CC=CC=1C1=CCOCC1 BYKSEVADXIBXTH-UHFFFAOYSA-N 0.000 claims 1
- XGMXDYRMLPAZKF-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C=2CCOCC=2)=N1 XGMXDYRMLPAZKF-UHFFFAOYSA-N 0.000 claims 1
- TVXURCBJJQDUAY-UHFFFAOYSA-N 1-[6-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC=C(C=3CCOCC=3)C=C2C=1NC(=O)NC1=CN=CC=N1 TVXURCBJJQDUAY-UHFFFAOYSA-N 0.000 claims 1
- VSAVKIVEYJZKSW-UHFFFAOYSA-N 1-[6-(oxan-3-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2COCCC2)=N1 VSAVKIVEYJZKSW-UHFFFAOYSA-N 0.000 claims 1
- VXQWZNGQNKCLKD-UHFFFAOYSA-N 1-[6-(oxan-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC(=CC=C3N=CC=2)C2CCOCC2)=N1 VXQWZNGQNKCLKD-UHFFFAOYSA-N 0.000 claims 1
- XFRYMFRHCLWJQY-UHFFFAOYSA-N 1-[6-(trifluoromethyl)pyridin-2-yl]-3-[7-(trifluoromethyl)quinolin-4-yl]urea Chemical compound C=1C=NC2=CC(C(F)(F)F)=CC=C2C=1NC(=O)NC1=CC=CC(C(F)(F)F)=N1 XFRYMFRHCLWJQY-UHFFFAOYSA-N 0.000 claims 1
- FBWWNLBZZFVRQY-UHFFFAOYSA-N 1-[6-(trifluoromethyl)pyridin-2-yl]-3-[8-(trifluoromethyl)quinolin-4-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=CC(=C3N=CC=2)C(F)(F)F)=N1 FBWWNLBZZFVRQY-UHFFFAOYSA-N 0.000 claims 1
- VBISSAFCYVKVAC-UHFFFAOYSA-N 1-[6-[1-(2,2-difluoroethyl)piperidin-4-yl]pyridin-2-yl]-3-(8-fluoroquinolin-4-yl)urea Chemical compound C1CN(CC(F)F)CCC1C1=CC=CC(NC(=O)NC=2C3=CC=CC(F)=C3N=CC=2)=N1 VBISSAFCYVKVAC-UHFFFAOYSA-N 0.000 claims 1
- DCHDMOPFMYEBSB-UHFFFAOYSA-N 1-[6-[1-(2,2-difluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(CC(F)F)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 DCHDMOPFMYEBSB-UHFFFAOYSA-N 0.000 claims 1
- HEFHJWMRPPVCTR-UHFFFAOYSA-N 1-[6-[1-(2-fluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound C1CN(CCF)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 HEFHJWMRPPVCTR-UHFFFAOYSA-N 0.000 claims 1
- XFPMVDJORHOMMD-UHFFFAOYSA-N 1-[6-[1-(2-fluoroethyl)piperidin-4-yl]quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C1CN(CCF)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 XFPMVDJORHOMMD-UHFFFAOYSA-N 0.000 claims 1
- NQGMRQWIVQLMHW-UHFFFAOYSA-N 1-[7-(3,4-dihydro-2h-pyran-5-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(C=C3N=CC=2)C=2CCCOC=2)=N1 NQGMRQWIVQLMHW-UHFFFAOYSA-N 0.000 claims 1
- NKOFCVPOYFPQHF-UHFFFAOYSA-N 1-[7-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(C=C3N=CC=2)C=2CCOCC=2)=N1 NKOFCVPOYFPQHF-UHFFFAOYSA-N 0.000 claims 1
- MUANCMSIGNOISO-UHFFFAOYSA-N 1-[7-(3,6-dihydro-2h-pyran-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC(C=3CCOCC=3)=CC=C2C=1NC(=O)NC1=CN=CC=N1 MUANCMSIGNOISO-UHFFFAOYSA-N 0.000 claims 1
- KWVPRRBJZGHPPP-UHFFFAOYSA-N 1-[7-(oxan-4-yl)quinolin-4-yl]-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=C(C=C3N=CC=2)C2CCOCC2)=N1 KWVPRRBJZGHPPP-UHFFFAOYSA-N 0.000 claims 1
- BSBUFEFSAHPKBI-UHFFFAOYSA-N 1-[7-(oxan-4-yl)quinolin-4-yl]-3-pyrazin-2-ylurea Chemical compound C=1C=NC2=CC(C3CCOCC3)=CC=C2C=1NC(=O)NC1=CN=CC=N1 BSBUFEFSAHPKBI-UHFFFAOYSA-N 0.000 claims 1
- OFHYJGIWOBCELM-UHFFFAOYSA-N 1-pyrazin-2-yl-3-(6-pyrrolidin-3-ylquinolin-4-yl)urea Chemical compound C=1C=NC2=CC=C(C3CNCC3)C=C2C=1NC(=O)NC1=CN=CC=N1 OFHYJGIWOBCELM-UHFFFAOYSA-N 0.000 claims 1
- COCKHBFAABWZBN-UHFFFAOYSA-N 1-pyrazin-2-yl-3-[6-(1,2,3,6-tetrahydropyridin-4-yl)quinolin-4-yl]urea Chemical compound C=1C=NC2=CC=C(C=3CCNCC=3)C=C2C=1NC(=O)NC1=CN=CC=N1 COCKHBFAABWZBN-UHFFFAOYSA-N 0.000 claims 1
- IEDGRSYITLMBAN-UHFFFAOYSA-N 1-quinolin-4-yl-3-[6-(trifluoromethyl)pyridin-2-yl]urea Chemical compound FC(F)(F)C1=CC=CC(NC(=O)NC=2C3=CC=CC=C3N=CC=2)=N1 IEDGRSYITLMBAN-UHFFFAOYSA-N 0.000 claims 1
- 125000001627 3 membered heterocyclic group Chemical group 0.000 claims 1
- 125000001963 4 membered heterocyclic group Chemical group 0.000 claims 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 208000036574 Behavioural and psychiatric symptoms of dementia Diseases 0.000 claims 1
- 208000020925 Bipolar disease Diseases 0.000 claims 1
- 239000005973 Carvone Substances 0.000 claims 1
- 208000010412 Glaucoma Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000017442 Retinal disease Diseases 0.000 claims 1
- 206010038923 Retinopathy Diseases 0.000 claims 1
- 201000004810 Vascular dementia Diseases 0.000 claims 1
- 230000001154 acute effect Effects 0.000 claims 1
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 206010008118 cerebral infarction Diseases 0.000 claims 1
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- 125000004438 haloalkoxy group Chemical group 0.000 claims 1
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims 1
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 1
- 125000002636 imidazolinyl group Chemical group 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 208000015122 neurodegenerative disease Diseases 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 208000033808 peripheral neuropathy Diseases 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 125000003072 pyrazolidinyl group Chemical group 0.000 claims 1
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- YCACGYUSNVXULM-UHFFFAOYSA-N tert-butyl 3-[4-(pyrazin-2-ylcarbamoylamino)quinolin-6-yl]-2,5-dihydropyrrole-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC=C1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 YCACGYUSNVXULM-UHFFFAOYSA-N 0.000 claims 1
- GZNADDRJCSQZJF-UHFFFAOYSA-N tert-butyl 3-[4-(pyrazin-2-ylcarbamoylamino)quinolin-6-yl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=CC=NC=3)C2=C1 GZNADDRJCSQZJF-UHFFFAOYSA-N 0.000 claims 1
- GBJYNPNJPWTFLR-UHFFFAOYSA-N tert-butyl 3-[4-[[6-(trifluoromethyl)pyridin-2-yl]carbamoylamino]quinolin-6-yl]-2,5-dihydropyrrole-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC=C1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=CC=3)C(F)(F)F)C2=C1 GBJYNPNJPWTFLR-UHFFFAOYSA-N 0.000 claims 1
- HJULFMJNYVIQIN-UHFFFAOYSA-N tert-butyl 4-[4-(pyrazin-2-ylcarbamoylamino)quinolin-6-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C3C(NC(=O)NC=4N=CC=NC=4)=CC=NC3=CC=2)=C1 HJULFMJNYVIQIN-UHFFFAOYSA-N 0.000 claims 1
- GIACGSWLXZCBGT-UHFFFAOYSA-N tert-butyl 4-[4-[(6-cyclopropylpyrazin-2-yl)carbamoylamino]quinolin-6-yl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CC=C(N=CC=C2NC(=O)NC=3N=C(C=NC=3)C3CC3)C2=C1 GIACGSWLXZCBGT-UHFFFAOYSA-N 0.000 claims 1
- YEJAFXVKMRTNJM-UHFFFAOYSA-N tert-butyl 4-[4-[[6-(trifluoromethyl)pyridin-2-yl]carbamoylamino]quinolin-6-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2C=C3C(NC(=O)NC=4N=C(C=CC=4)C(F)(F)F)=CC=NC3=CC=2)=C1 YEJAFXVKMRTNJM-UHFFFAOYSA-N 0.000 claims 1
- PKQSFTTUFQKADK-UHFFFAOYSA-N tert-butyl 4-[6-[(8-fluoroquinolin-4-yl)carbamoylamino]pyridin-2-yl]-3,6-dihydro-2h-pyridine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC(C=2N=C(NC(=O)NC=3C4=CC=CC(F)=C4N=CC=3)C=CC=2)=C1 PKQSFTTUFQKADK-UHFFFAOYSA-N 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 125000004853 tetrahydropyridinyl group Chemical group N1(CCCC=C1)* 0.000 claims 1
- 125000002053 thietanyl group Chemical group 0.000 claims 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201061428478P | 2010-12-30 | 2010-12-30 | |
| US61/428,478 | 2010-12-30 | ||
| US201161521868P | 2011-08-10 | 2011-08-10 | |
| US61/521,868 | 2011-08-10 | ||
| PCT/EP2011/074272 WO2012089828A2 (en) | 2010-12-30 | 2011-12-30 | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017011851A Division JP2017122089A (ja) | 2010-12-30 | 2017-01-26 | 複素環化合物およびグリコーゲンシンターゼキナーゼ−３阻害薬としてのそれの使用 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014501269A JP2014501269A (ja) | 2014-01-20 |
| JP2014501269A5 true JP2014501269A5 (enrdf_load_stackoverflow) | 2015-02-19 |
| JP6144201B2 JP6144201B2 (ja) | 2017-06-07 |
Family
ID=45524498
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2013546715A Expired - Fee Related JP6144201B2 (ja) | 2010-12-30 | 2011-12-30 | 複素環化合物およびグリコーゲンシンターゼキナーゼ−３阻害薬としてのそれの使用 |
| JP2017011851A Pending JP2017122089A (ja) | 2010-12-30 | 2017-01-26 | 複素環化合物およびグリコーゲンシンターゼキナーゼ−３阻害薬としてのそれの使用 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2017011851A Pending JP2017122089A (ja) | 2010-12-30 | 2017-01-26 | 複素環化合物およびグリコーゲンシンターゼキナーゼ−３阻害薬としてのそれの使用 |
Country Status (15)
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MX2009004140A (es) * | 2006-10-21 | 2009-07-10 | Abbott Gmbh & Co Kg | Compuestos heterociclicos y su uso como inhibidores de la glucogeno sintasa quinasa 3. |
| WO2012041814A1 (en) | 2010-09-27 | 2012-04-05 | Abbott Gmbh & Co. Kg | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| US9090592B2 (en) * | 2010-12-30 | 2015-07-28 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| JP6534098B2 (ja) * | 2014-09-12 | 2019-06-26 | 国立大学法人 鹿児島大学 | 成人ｔ細胞白血病治療薬 |
| US11248007B2 (en) * | 2017-03-08 | 2022-02-15 | Cornell University | Inhibitors of MALT1 and uses thereof |
| RU2739489C2 (ru) * | 2018-03-06 | 2020-12-24 | Закрытое Акционерное Общество "Биокад" | Новые гетероциклические соединения как ингибиторы CDK8/19 |
| AU2019359823B2 (en) * | 2018-10-17 | 2025-07-10 | Duke University | Quinone reductase 2 inhibitors for use as neuroprotective agents |
| AU2020218366A1 (en) | 2019-02-08 | 2021-09-16 | Frequency Therapeutics, Inc. | Valproic acid compounds and Wnt agonists for treating ear disorders |
| KR20220097418A (ko) * | 2019-11-01 | 2022-07-07 | 신젠타 크롭 프로텍션 아게 | 살충 활성 융합된 바이사이클릭 이종방향족 화합물 |
| WO2021257857A1 (en) | 2020-06-19 | 2021-12-23 | Incyte Corporation | Naphthyridinone compounds as jak2 v617f inhibitors |
| US11753413B2 (en) | 2020-06-19 | 2023-09-12 | Incyte Corporation | Substituted pyrrolo[2,1-f][1,2,4]triazine compounds as JAK2 V617F inhibitors |
| CR20230057A (es) | 2020-07-02 | 2023-08-15 | Incyte Corp | Compuestos tríciclicos de urea como inhibidores de jak2 v617f |
| WO2022006456A1 (en) | 2020-07-02 | 2022-01-06 | Incyte Corporation | Tricyclic pyridone compounds as jak2 v617f inhibitors |
| WO2022046989A1 (en) | 2020-08-27 | 2022-03-03 | Incyte Corporation | Tricyclic urea compounds as jak2 v617f inhibitors |
| US11919908B2 (en) | 2020-12-21 | 2024-03-05 | Incyte Corporation | Substituted pyrrolo[2,3-d]pyrimidine compounds as JAK2 V617F inhibitors |
| US11958861B2 (en) | 2021-02-25 | 2024-04-16 | Incyte Corporation | Spirocyclic lactams as JAK2 V617F inhibitors |
| US12084430B2 (en) | 2022-03-17 | 2024-09-10 | Incyte Corporation | Tricyclic urea compounds as JAK2 V617F inhibitors |
Family Cites Families (66)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MY115155A (en) | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
| AU6964096A (en) | 1995-09-15 | 1997-04-01 | Pharmacia & Upjohn Company | Aminoaryl oxazolidinone n-oxides |
| AUPP003197A0 (en) * | 1997-09-03 | 1997-11-20 | Fujisawa Pharmaceutical Co., Ltd. | New heterocyclic compounds |
| US20030220234A1 (en) | 1998-11-02 | 2003-11-27 | Selvaraj Naicker | Deuterated cyclosporine analogs and their use as immunodulating agents |
| CN1312807A (zh) | 1998-06-19 | 2001-09-12 | 希龙公司 | 糖元合成酶激酶3的抑制剂 |
| UA73492C2 (en) * | 1999-01-19 | 2005-08-15 | Aromatic heterocyclic compounds as antiinflammatory agents | |
| GB9918037D0 (en) | 1999-07-30 | 1999-09-29 | Biochemie Gmbh | Organic compounds |
| US6387900B1 (en) | 1999-08-12 | 2002-05-14 | Pharmacia & Upjohn S.P.A. | 3(5)-ureido-pyrazole derivatives process for their preparation and their use as antitumor agents |
| GT200100147A (es) | 2000-07-31 | 2002-06-25 | Derivados de imidazol | |
| BR0113574A (pt) | 2000-08-31 | 2003-07-22 | Pfizer Prod Inc | Derivados de pirazol e uso dos mesmos como inibidores de proteìna quinase |
| WO2002022603A1 (en) | 2000-09-15 | 2002-03-21 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| HUP0400067A2 (hu) | 2001-04-30 | 2004-04-28 | Zentaris Gmbh | Dementia és neurodegeneratív betegségek kezelése közepes dózisú LHRH-antagonistával |
| DE10123586A1 (de) | 2001-05-08 | 2002-11-28 | Schering Ag | 3,5-Diamino-1,2,4-triazole als Kinase Inhibitoren |
| ES2254611T3 (es) | 2001-05-11 | 2006-06-16 | Pfizer Products Inc. | Derivados de tiazol. |
| SE0102439D0 (sv) | 2001-07-05 | 2001-07-05 | Astrazeneca Ab | New compounds |
| BR0213562A (pt) | 2001-10-26 | 2004-08-31 | Aventis Pharma Inc | Benzimidazóis e análogos e seu uso como inibidores de cinases de proteìna |
| WO2003049739A1 (en) | 2001-12-07 | 2003-06-19 | Vertex Pharmaceuticals, Inc. | Pyrimidine-based compounds useful as gsk-3 inhibitors |
| SE0104341D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New use |
| SE0104340D0 (sv) | 2001-12-20 | 2001-12-20 | Astrazeneca Ab | New compounds |
| TW200301123A (en) | 2001-12-21 | 2003-07-01 | Astrazeneca Uk Ltd | New use |
| EP1458711B1 (en) | 2001-12-21 | 2007-07-18 | AstraZeneca AB | Use of oxindole derivatives in the treatment of dementia related diseases, alzheimer s disease and conditions associated with glycogen synthase kinase-3 |
| SE0200979D0 (sv) | 2002-03-28 | 2002-03-28 | Astrazeneca Ab | New compounds |
| US7601718B2 (en) | 2003-02-06 | 2009-10-13 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of protein kinases |
| CA2532965C (en) | 2003-07-22 | 2013-05-14 | Astex Therapeutics Limited | 3, 4-disubstituted 1h-pyrazole compounds and their use as cyclin dependent kinases (cdk) and glycogen synthase kinase-3 (gsk-3) modulators |
| AU2004267094A1 (en) | 2003-08-20 | 2005-03-03 | Vertex Pharmaceuticals Incorporated | (4 -amino -1,2, 5-oxadiazol-4-yl) -hetxiroaromatic compounds useful as protein kinase inhibitors |
| EP1689753A4 (en) | 2003-12-04 | 2010-07-07 | Glaxosmithkline Llc | NEW CHEMICAL COMPOUNDS |
| EP1694686A1 (en) | 2003-12-19 | 2006-08-30 | Takeda San Diego, Inc. | Kinase inhibitors |
| EP1586318A1 (en) | 2004-04-05 | 2005-10-19 | Neuropharma S.A.U. | Thiadiazolidinones as GSK-3 inhibitors |
| EP1737850B1 (en) | 2004-04-19 | 2007-10-03 | Symed Labs Limited | A novel process for the preparation of linezolid and related compounds |
| EP1781293A1 (en) | 2004-06-04 | 2007-05-09 | Amphora Discovery Corporation | Quinoline- and isoquinoline-based compounds exhibiting atp-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| US20080153869A1 (en) | 2004-06-14 | 2008-06-26 | Bressi Jerome C | Kinase Inhibitors |
| EP1781653A1 (en) | 2004-07-05 | 2007-05-09 | Astex Therapeutics Limited | 3,4-disubstituted pyrazoles as cyclin dependent kinases (cdk) or aurora kinase or glycogen synthase 3 (gsk-3) inhibitors |
| WO2006008754A1 (en) | 2004-07-20 | 2006-01-26 | Symed Labs Limited | Novel intermediates for linezolid and related compounds |
| US7511013B2 (en) | 2004-09-29 | 2009-03-31 | Amr Technology, Inc. | Cyclosporin analogues and their pharmaceutical uses |
| WO2006091737A1 (en) | 2005-02-24 | 2006-08-31 | Kemia, Inc. | Modulators of gsk-3 activity |
| TW200716636A (en) | 2005-05-31 | 2007-05-01 | Speedel Experimenta Ag | Heterocyclic spiro-compounds |
| JP5345388B2 (ja) | 2005-06-30 | 2013-11-20 | ジヤンセン・フアーマシユーチカ・ナームローゼ・フエンノートシヤツプ | 環式アニリノ−ピリジノトリアジン |
| EP1749523A1 (en) | 2005-07-29 | 2007-02-07 | Neuropharma, S.A. | GSK-3 inhibitors |
| US7514068B2 (en) | 2005-09-14 | 2009-04-07 | Concert Pharmaceuticals Inc. | Biphenyl-pyrazolecarboxamide compounds |
| AR055669A1 (es) | 2005-10-03 | 2007-08-29 | Astrazeneca Ab | Derivados de 3h - imidazo[4, 5 -b]piridina como inhibidores selectivos de gsk3, metodos e internediarios para su preparacion, composiciones farmaceuticas que los contienen y su uso para la elaboracion de un medicamento para el tratamiento de enfermedades neurodegenerativas y mentales. |
| CA2637392A1 (en) | 2006-01-23 | 2007-07-26 | Crystalgenomics, Inc. | Imidazopyridine derivatives inhibiting protein kinase activity, method for the preparation thereof and pharmaceutical composition containing same |
| EP1981500A4 (en) | 2006-02-02 | 2010-08-25 | Astrazeneca Ab | PHARMACEUTICAL USE OF 2-HYDROXY-3- [5- (MORPHOLIN-4-YLMETHYL) PYRIDINE-2-YL] -1H-INDOL-5-CARBONITRIL AS FREE BASE OR SALT |
| WO2007120102A1 (en) | 2006-04-19 | 2007-10-25 | Astrazeneca Ab | New substituted oxindole derivatives |
| EP1849785A1 (en) | 2006-04-28 | 2007-10-31 | Neuropharma, S.A. | N-(2-Thiazolyl)-amide derivatives as GSK-3 inhibitors |
| US7622495B2 (en) | 2006-10-03 | 2009-11-24 | Neurim Pharmaceuticals (1991) Ltd. | Substituted aryl-indole compounds and their kynurenine/kynuramine-like metabolites as therapeutic agents |
| MX2009004140A (es) * | 2006-10-21 | 2009-07-10 | Abbott Gmbh & Co Kg | Compuestos heterociclicos y su uso como inhibidores de la glucogeno sintasa quinasa 3. |
| US8796267B2 (en) | 2006-10-23 | 2014-08-05 | Concert Pharmaceuticals, Inc. | Oxazolidinone derivatives and methods of use |
| MX2009006690A (es) | 2006-12-19 | 2009-07-31 | Vertex Pharma | Aminopirimidinas utiles como inhibidores de proteinas cinasas. |
| ES2446269T3 (es) | 2006-12-19 | 2014-03-06 | The Board Of Trustees Of The University Of Illinois | 3-Benzofuranil-4-indolil-maleimidas como potentes inhibidores de GSK-3 para trastornos neurodegenerativos |
| MX2009008465A (es) | 2007-02-15 | 2009-08-20 | Hoffmann La Roche | Nuevas 2-aminooxazolinas como ligandos de taar1. |
| CN101679353A (zh) | 2007-04-18 | 2010-03-24 | 阿斯利康(瑞典)有限公司 | 制备化合物2-羟基-3-[5-(吗啉-4-基甲基)吡啶-2-基]1h-吲哚-5-腈701的新方法 |
| CN101687824A (zh) | 2007-04-19 | 2010-03-31 | 康塞特医药品公司 | 氘化吗啉基化合物 |
| EP1992624A1 (en) | 2007-05-16 | 2008-11-19 | Sanofi-Aventis | Heteroarylamide pyrimidone compounds |
| US7531685B2 (en) | 2007-06-01 | 2009-05-12 | Protia, Llc | Deuterium-enriched oxybutynin |
| EP2167491A1 (en) * | 2007-06-08 | 2010-03-31 | Abbott Laboratories | 5-heteroaryl substituted indazoles as kinase inhibitors |
| WO2009035598A1 (en) | 2007-09-10 | 2009-03-19 | Concert Pharmaceuticals, Inc. | Deuterated pirfenidone |
| US20090118238A1 (en) | 2007-09-17 | 2009-05-07 | Protia, Llc | Deuterium-enriched alendronate |
| US20090082471A1 (en) | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched fingolimod |
| US20090088416A1 (en) | 2007-09-26 | 2009-04-02 | Protia, Llc | Deuterium-enriched lapaquistat |
| JP2010540635A (ja) | 2007-10-02 | 2010-12-24 | コンサート ファーマシューティカルズ インコーポレイテッド | ピリミジンジオン誘導体 |
| US20090105338A1 (en) | 2007-10-18 | 2009-04-23 | Protia, Llc | Deuterium-enriched gabexate mesylate |
| US8410124B2 (en) | 2007-10-18 | 2013-04-02 | Concert Pharmaceuticals Inc. | Deuterated etravirine |
| WO2009055006A1 (en) | 2007-10-26 | 2009-04-30 | Concert Pharmaceuticals, Inc. | Deuterated darunavir |
| EP2297154B1 (en) * | 2008-04-24 | 2013-04-03 | Abbott GmbH & Co. KG | 1- (7-(hexahydropyrrolo [3, 4-c]pyrrol-2 (1h) -yl) quin0lin-4-yl) -3- (pyrazin-2-yl) urea derivatives and related compounds as glycogen synthase kinase 3 (gsk-3) inhibitors |
| TW201040191A (en) | 2009-03-27 | 2010-11-16 | Abbott Gmbh & Co Kg | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
| US9090592B2 (en) * | 2010-12-30 | 2015-07-28 | AbbVie Deutschland GmbH & Co. KG | Heterocyclic compounds and their use as glycogen synthase kinase-3 inhibitors |
-
2011
- 2011-12-29 US US13/339,884 patent/US9090592B2/en not_active Expired - Fee Related
- 2011-12-30 KR KR1020137020021A patent/KR101860297B1/ko not_active Expired - Fee Related
- 2011-12-30 AU AU2011351375A patent/AU2011351375B2/en not_active Ceased
- 2011-12-30 CA CA2821863A patent/CA2821863A1/en not_active Abandoned
- 2011-12-30 JP JP2013546715A patent/JP6144201B2/ja not_active Expired - Fee Related
- 2011-12-30 NZ NZ611314A patent/NZ611314A/en not_active IP Right Cessation
- 2011-12-30 CN CN201180068418.0A patent/CN103476766B/zh not_active Expired - Fee Related
- 2011-12-30 SG SG2013050703A patent/SG191789A1/en unknown
- 2011-12-30 WO PCT/EP2011/074272 patent/WO2012089828A2/en active Application Filing
- 2011-12-30 EP EP17206645.8A patent/EP3351543A1/en not_active Withdrawn
- 2011-12-30 RU RU2013135477A patent/RU2623427C2/ru not_active IP Right Cessation
- 2011-12-30 MX MX2013007702A patent/MX336346B/es unknown
- 2011-12-30 EP EP11811357.0A patent/EP2658854B1/en not_active Not-in-force
- 2011-12-30 BR BR112013016928-1A patent/BR112013016928A2/pt not_active IP Right Cessation
- 2011-12-30 SG SG10201406098UA patent/SG10201406098UA/en unknown
-
2013
- 2013-05-30 IL IL226676A patent/IL226676A/en active IP Right Grant
- 2013-06-25 ZA ZA2013/04756A patent/ZA201304756B/en unknown
-
2015
- 2015-06-15 US US14/740,048 patent/US9540370B2/en not_active Expired - Fee Related
-
2017
- 2017-01-26 JP JP2017011851A patent/JP2017122089A/ja active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2014501269A5 (enrdf_load_stackoverflow) | ||
| RU2013135477A (ru) | Гетероциклические соединения и их применение в качестве ингибиторов киназы-3 гликогенсинтазы | |
| KR101819433B1 (ko) | 인돌린-2-온 또는 피롤로-피리딘-2-온 유도체 | |
| JP2010524974A5 (enrdf_load_stackoverflow) | ||
| KR20210103498A (ko) | 메티오닌 아데노실트랜스퍼라제 2a 억제제로서 2-옥소퀴나졸린 유도체 | |
| KR102002265B1 (ko) | 바이헤테로아릴 화합물 및 이의 용도 | |
| RU2014139601A (ru) | Ингибиторы серин/треониновых киназ | |
| SI3083586T1 (en) | The new carboxamides, the process of their manufacture, the pharmaceutical preparations they contain and their use for the manufacture of medicinal products | |
| JP2013544256A5 (enrdf_load_stackoverflow) | ||
| RU2012136643A (ru) | [5,6]- гетероциклическое соединение | |
| RU2507204C2 (ru) | Положительные аллостерические модуляторы м1-рецепторов на основе пираниларилметилбензохиназолинона | |
| RU2016118619A (ru) | Селективно замещенные соединения хинолина | |
| JP2006509715A5 (enrdf_load_stackoverflow) | ||
| JP2019523233A5 (enrdf_load_stackoverflow) | ||
| RU2013124101A (ru) | Гетероциклические амины и их применения | |
| JP2015500332A5 (enrdf_load_stackoverflow) | ||
| JP2014521711A5 (enrdf_load_stackoverflow) | ||
| RU2011136825A (ru) | Производные аминопиразина и лекарственные средства | |
| RU2018142987A (ru) | Положительные аллостерические модуляторы мускаринового ацетилхолинового рецептора m4 | |
| JP2016535003A5 (enrdf_load_stackoverflow) | ||
| CA2351725A1 (en) | Substituted pyrazoles as p38 kinase inhibitors | |
| JP2012508776A5 (enrdf_load_stackoverflow) | ||
| JP2010524970A5 (enrdf_load_stackoverflow) | ||
| RU2015100942A (ru) | Производное пиперидинилпиразолпиридина | |
| JP2015503571A5 (enrdf_load_stackoverflow) |